Oops! I ruined your life. :)

It was one of those, “please, please, let this send,” kind of moments when you hope a weak airport WiFi connection doesn’t disconnect, a low-battery indicator doesn’t shut down your laptop — who knows where there’s an outlet in this airport — and your email actually sends to your million dollar client when the message popped up and your stomach drops: “Oops!”

Like some kind of creepy, American Psycho moment, a hardly-discernible, non-apologetic message from Gmail put this exact dagger into my heart and sent me wondering what went wrong.

Sure, of course, just lemme look up error #001. What?

Google’s Chrome browser gives off an even worse error message that doesn’t make things better, just a wanna-be-hipster-piece-of-software knocking off a Susan Kare classic laughing in your face when you’re frustrated:

Maybe this is part of some awful brand initiative. After all, Google is a place of smiles. An every-color-of-the-rainbow logo, and three square meals place to work with unbelievable benefits. But, then again, Google is hardly alone in this kind of “smile when you’ve fallen” approach to error messages.

Microsoft is sadly considering implementing the same, cutesy thinking in a revamp of their blue screen of death as a part of their otherwise exciting, new Windows 8 operating system:

Fortunately, Microsoft offers some advice. Just search for the error message, “HAL_INITIALIZATION_FAILED”…oh wait, this is the blue screen of death. My computer is totally effed.

Not to be oops-outdone by Google, Microsoft’s XBox website includes the word, “Oops!” twice in an error message, first in the header and then as the first word to explain the header. Obviously, after frustrating someone, the best thing to do is say “Oops!” over and over again.

Sure, I’ll “like” that page.

And if you thought the non-profit Mozilla Foundation avoided this kind of creepy, cutesy error messaging in their Firefox browser, you thought wrong.

The legoman is sorry that you can’t load your favorite TV show.

In times like this, there’s always YouTube, right? Millions of fun videos to help us laugh at times of stress.

You know, not too long ago, whenever something in software was confusing to users, software-makers had a brilliant, can’t fail, simple solution: add a how-to in the help section. Instead of spending hours making strange features straightforward, software companies passed the buck to the user: “Um, we can’t figure out how to make it easy to do, so just read the manual.”

Now it seems like there is another, new kind of awful simple solution for glitches and errors that infuriate people: a cutesy smiley face. After all, no one cares if you ruin their life as long as you do it with a smile, right?

The root of Oops!

In 1925, a New Yorker cartoon caption is credited with being the first published instance of “Whoopsie Daisy!” But the real root of the “oops” phenomenon in software might be pointed to the Linux operating system.

Upon “a bug in the kernel” Linux kicks back an OOPS error message. First developed in 1991, Linux’s code for error messages may have crept into the developer’s subconscious eventually leading to today’s proliferation of “oops.” Here’s an example:

But now that they are a publicly traded, 186 billion dollar company that we rely on for important business communications, which could make or break jobs, their cute error messages are about as cute as a Bill Gates tossing floppy disks. In other words, just plain creepy.

Turn it down from 11

The language of error messages in old software like MS-DOS were notoriously unfriendly.

But today’s insulting cutesy error message writers have swung the pendulum too far. A common recommendation to use natural language to turn an incomprehensible “Error: Stack Overflow” has not turned into something polite and understandable, but instead an insulting “Oops! Aw, snap!”

What we need to do is dial it down from 11 on the friendly meter…11 is just too creepy. There is a happy middle ground where developers can apologize and software can provide the user polite guidance about what to do next. Website, app, software, you screwed up; help the user get their desired task completed ASAP.

To paraphrase Jon Stewart, oops is not the four letter word I would have chosen.

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